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Email Stuck in Outlook 2010 outbox

Question

First let me say that I use Outlook 2010 and for the most part I am VERY happy with it. But yesterday I was sending emails with attachments and 4 out of the 8 that I sent are still stuck in the outbox. If I send other emails that do not have attachments it is still taking a long time for them to go through. I have now had to go to my hotmail account to send mail (which is what I did not want to do since I use Outlook) so that it can bypass the stuck emails. Is there a way to move/delete something to get them gone so that I can send mail like before?

I understand that you are unable to send emails in Outlook 2010. The emails got stuck in the Outbox.

Based on the current situation, this issue can be caused by several factors, such as Internet connection, Outlook settings or corrupted outlook profile. We can try the following methods to see if the problem can be resolved.

Method 1:

====================

Click the “Send/Receive” tab, then click “Send all”.

Method 2: New Outlook profile

==============

1.Exit Outlook.

2.Go to Start > Control Panel, click or double-click Mail.

Mail appears in different Control Panel locations depending upon the version of the Microsoft Windows operating system, Control Panel view selected, and whether a 32- or 64-bit operating system or version of Outlook is installed.

The easiest way to locate Mail is to open Control Panel in Windows, and then in the Search box at the top of window, type Mail. In Control Panel for Windows XP, type Mail in the Address box.

NoteThe Mail icon appears after Outlook starts for the first time.

The title bar of the Mail Setup dialog box contains the name of the current profile. To select a different existing profile, click Show Profiles, select the profile name, and then click Properties.

I understand that you are unable to send emails in Outlook 2010. The emails got stuck in the Outbox.

Based on the current situation, this issue can be caused by several factors, such as Internet connection, Outlook settings or corrupted outlook profile. We can try the following methods to see if the problem can be resolved.

Method 1:

====================

Click the “Send/Receive” tab, then click “Send all”.

Method 2: New Outlook profile

==============

1.Exit Outlook.

2.Go to Start > Control Panel, click or double-click Mail.

Mail appears in different Control Panel locations depending upon the version of the Microsoft Windows operating system, Control Panel view selected, and whether a 32- or 64-bit operating system or version of Outlook is installed.

The easiest way to locate Mail is to open Control Panel in Windows, and then in the Search box at the top of window, type Mail. In Control Panel for Windows XP, type Mail in the Address box.

NoteThe Mail icon appears after Outlook starts for the first time.

The title bar of the Mail Setup dialog box contains the name of the current profile. To select a different existing profile, click Show Profiles, select the profile name, and then click Properties.

forgot to mention that aprox 90% of our users are still using Outlook 2003 - they do not experince any problems - our mail server i exchange 2010 - I know the protocol used by clients to communicate with the server is different from 2003 to 2010, so giving
the fack that Outlook 2003 does not have problems, does not exclude the server from having configurations isues

I do how-ever admit that the most likly place to look is at the client side (since it works for some users)

None of our Outlook 2010 kcients are installede by hand, they are all pushed to the client the same way, so they should behaive the same....

I have the same problem...Outlook 2010 client but using Exchange 2003 on the back end. Outbox slows to a crawl. The best way I have found to resolve is to restart Outlook and the mail goes out right away. I have recreated my profile
with no difference.

Another problem I have is that getting Free Busy Info for meeting attendees is spotty...sometime it is immediate, sometimes takes forever, other times it never loads.

I had the problem of stuck email with photo attachments, regardless of file size, being stuck in Outlook 2010 Outbox. Your suggestion to use Work Offline worked but only after leaving Outlook 2010 in the Work Offline for many, many minutes.
Then I was able to go back to the Outbox in the Home Tab and click on the Bib "X" Delete button. The file was deleted. I then delted the file from the Deleted Items Folder, closed Outlook 2010 and reopened to be safe. I am trusting this will
fix the problem if it occures in the future. I never had a problem sending email with any attachments with any version of Outlook since Outlook was firs introduced by MS. Outlook 2010 has caused some grey hair since I loaded Office 2010 Professional.

I recommend first trying the method that Ben M. Schoor suggests above using the Work Offline. I had to wait several minutes after going to Work Offline before being able to delete the Stuck outbox message. Besure to get out of Work Offline,
back to Normal Outlook operaton. Also, recommend deleting the problem stuck message from the Deleted Folder and closing Outlook 2010 and then reopen the Outlook 2010.

Trying to create a New Outlok Profile will lead you into problems unless you are very familiar with backing up you Outlook 2010 and reconfiguring all your email addresses, etc. Doing this method you might as well remove Outlook 2010 which means removing
Office 2010 suite. Try to avoid this method of creating a New Outlook Profile for any version of Outlook.

I just want to add that I am experiencing this exact problem others are describing in this thread, with the main difference that I seldom send any large attachments so this happens even to tiny e-mails.

Normally everything works perfectly but then sometimes I can find there are e-mails waiting in the Outbox to be sent. These can be replies or "new" mails, doesn't matter. I am fully connected to Exchange when it happens and "All folders are up
to date."If I do a Send / Receive All (F9) it just says Sending is "Completed".

I tried going into "Work Offline" to let the connections to Exchange disconnect. Then connected again, but this did in fact not help me. Sometimes I've been able to double-click the e-mail, press Send and it went away, but very seldom it works.

Safest way to get it back working is to exit Outlook and re-start. It's quite frustrating though when you send a quick reply, start working on something else and come back to discover your reply never went away.

I'm running Windows 7 64-bit with Outlook 2010 32-bit. I am connected to an Exchange 2007 server and freshly re-synced my complete profile a week ago to see if that could mitigate the problem, which it didn't.

Only thing I can suggest is to open Outlook 2010 w/o connecting to the Exchange. Then go into Work Offline with Outlook 2010, delete the messages stuck in the Outbox (you may have to wait a few minutes to do the delete just as I had to wait - why,
I do not know), delete these messages from the Deleted foulder. Close Outlook. Shut down the PC and reboot. Open Outlook and go back to Working Online. Try sending a message with an attachment to besure Outlook 2010 has reset itself
to normal operation.

The other solution given to me was to remove Outlook 2010 or Office 2010 Suite; besure to backup Outlook first (the .pst Folders & Files) and deactivate Office 2010 if you need to remove Office 2010. Hope you do not have to do this procedure
as it is time consumming.

In fact the message is not stuck such as that I cannot remove it, it is just stuck in the sense that it won't be sent away from the outbox, so I think our problems may be a little different.

Something I noticed today is that out of my two Exchange accounts this can happen just to one of them and as soon as I restart the application it is solved, but it is very very frustrating to be in a situation such as this.

I have the exact same problem as Alex. I cannot use the 64-bit version of Office because Outlook 2010 64bit will not sync Windows Mobile devices. if anyone has any other suggestions it would be great. Rebooting every PC each time this happens is getting
to be a problem.

This is absurd... and very complicated. Why doesn't it just work???? Is there a glich in the microsoft program? I have trouble with microsoft....and call iyogi and all their techs are busy....I paid a small fortune for my brand new studio 15 laptop,
and now it doesn't work???????

We have exchange 2007 running and the only user using outlook 2010 is having 'Disconnected from Exchange ' and 'trying to connect ' as status whenever he uses outlook outside the company network. He can receive emails smoothly but while sending emails, they
tend to sit in outbox and go randomly after a restart of machine or the application. outlook 2010 within the domain is muh more stable then whiel being used outside the network .

I have a message that is 38 MB that is stuck and it won't send and it won't delete. When I try to open it, it says that it has already begun transmitting. This suggestion didn't work. Do you have any more suggestions? Thanks.

i've discovered work arounds but that is annoying. I recently was using 2007 on my laptop and didn't have these issues. I don't mind troubleshooting although for now i may just uninstall 2010. any fixes appreciated.

I have been dealing with this problem for some time. I work with executives and "workarounds" are not an option any longer. It makes me look bad because they think Microsoft wouldn't put out a product that doesn't work and "I" must be
the one who is at fault.

I delete the profile and add it back in and everything works for a "while", then it may happen again randomly. The problem with this is that they may not notice that their outbox isn't sending emails and much of what they do is time sensitive.
After I recreate their profile rarely am I able to resend the hung messages again and usually have to tell them to delete everything in the outbox and then recreate them. It's like the messages are corrupted and hang any subsequent emails from sending. This
again is not met with cooperation...

I would rather not deploy any new software MS releases until there is at least the first service pack but the executives want the latest and greatest the day it comes out. I have searched the internet exhaustively for a solution, hotfix, trick to fix this
that would be "invisible" to the user but have found none.

I am ready to open a ticket with MS but it would seem to me that if that was successful someone would have posted the results of that solution. I don't know why everyone here automaticly thinks of workarounds and the MS techs suggest workarounds when the
software should just work and the responsiblity is on MS... I have a typical deployment Outlook 2010 on mostly XP & Win7 with an Exchange 2007 server. It's not anything that should raise issues...

If anyone has a fix or an invisible "reliable" workround I would appreciate the info. I would also like to encourage MS to send out a hotfix with this since I have experienced this issue with multiple clients in varying configurations so it's obviously
a glitch. Other issues with Adobe add-ins and add-ins in general crashing out Outlook are annoying but since they involve different vendors I can accept the probability. Office 2010 is great but this one "little" problem is becoming a deal-breaker...

I've think I found a simple workaround to this problem for Outlook 2010. Go to the Options panel, then the Advanced option and check the box that says "SEND IMMEDIATELY WHEN CONNECTED" in the Send/Receive option. I tested this and it worked
GREAT. No more problem of emails getting stuck in the OUT folder with a "DATE: NONE". If you can live with your emails being sent immediately when clicking send, this is the perfect solution to this problem. wendell simmons

I tried fiddling around but the only way it would clear for sure was if I disconnected from the internet completely. I have now put my mail 2010, to send immediately, This should help, I am not sure what caused my problem. I have two thoughts one the address
I was sending to was NOT quite right it had a ' in it. and or the file was just to big. So pull the power cord from the router and shut down I waited 5 minutes you may get away with a shorter time. Then I fired her up opened mail and deleted the file I thought
was the problem and the others went through OK. Hope this helps RonB

there are two issues. If you try to send an attachemnt that is to big it will get stuck. Go offline and you should be able to delete it.

the other issue which has carried over from outlook 2007 is that emails just stay in the outbox and do not send. You can move them into drafts or your inbox and open them and send them again but unfortunately for me and others it usually occurs when
you do a mail merge (manually opening and sending 400 emails takes the efficiency out of things.

The send instantly fuctions works but sometimes i want to add attachemnts to my mail merges so I want access befor i send/receive. (adding attachments seems to make the stuck email issue worse)

The problem we are encountering is more general and more pervasive. We are using Outlook 2010 against Google Mail POP & SMTP servers (both generic gmail & Google Apps).

Virutally all mail sent stays in the outbox for an indeterminate amount of time. We have tried all the solutions suggested in this thread prior to this date and none work. If we set "Send immediately" it still waits. We try send/receive
- completes "successfully", but the mail is still in the outbox. We go offline, online, offline, online - still stuck. We set it to send/receive every 3 minutes - 20 minutes later it'll still be in the outbox. We turned off mail scanning on the anti-virus
(AVAST!) - made no difference.

Eventually, all mail does get sent. Just not when we want it. It might be 10 minutes later or two hours later or something in-between. This is extremely frustrating, as you can imagine.

It has nothing to do with Exchange, as there is no Exchange in the equation here - only Outlook 2010 and SMTP.

It seems that some flag in Outlook is not getting set to make it actually process the outbox. Send/receive
thinks it's doing its job, but it isn't.

The one thing we have not tried yet is the suggested freeware referenced by Alexey Kuznetsov on 12/10/2010 - I will research for reviews of it before attempting. If anyone has had good (or bad) experience with it - or any other solution, I'd appreciate hearing
about it.

firstly my outlook 2010 works well for the most part. but i face a problem 'intermittently' with only 'mails that i reply to'. this occurs when i reply to a company drafted template/mail (e.g. a mail with an interview
confirmation). the mail is stuck in my outbox but the recipient keeps receiving the mail until i delete the mail from my outbox. the issue has occurred randomly with atleast 5 different companies. some had attachments and some were just one-liner replies.
i have a godaddy account configured on my outlook. called them up and they said that if i am able to send mails from their internet interface (which i was able to without any trouble) and the issues occur intermittently, the issue is do with outlook. i have
deleted both the account settings and the data file and re-created them. problem seemed to have gone away but it resurfaced when i replied to a recent mail to a company.any help is appreciated

I also had similar problem mail stuck in outbox with deafult mail delivery set to PST on users with outlook 2010 and Exchange 2010.

I Installed the latest hotfix from Micorosoft. after that its working fine for our users..mails now not getting stuck in outbox..This hotfix not directly addressing this issue however it solved my problem..

I also get this sort of behaviour once in a while. When I try to close and open Outlook 2010 it does not seem to help. But if I restart Windows 7 (64) it seems to clear something up. As soon as I start Outlook after restart, all the e-mails are sent immediatly.
Not an elegant solution but it works.

Tried that, no luck. And when I try to click on and open the offending email I get an error dialogue: 'Cannot open this item. Outlook has already begun transmitting this message.' I get the same whether online or offline.

Great, simple answer that worked perfectly in Outlook 2010. I had a 14 mb file stuck, and i had gone offline, but didn;t realize "delete" would save the day. it was an urgent legal item and I'm grateful for this guidance.

I’ve been struggling with this issue for some time. I finally noticed that the issue occurred with only certain email addresses on the exchange –
If you delete all of your autocomplete entries and then re-add them it may solve your issue as it did for me.

I had this problem. I have just now realized that it is because of the companies logos etc included. Go to Options > Mail > Replies, in the drop down choose "Do not include Original Message when replying" or something like that.

I've had a similar problem on many stations I recently upgrade to Office 2010 from Office 2007. In every instance so far when someone has this problem I check their account settings and find two seperate Email accounts pointing to my Exchange server.
Once named default and the other named Microsoft Exchange.

Now if I go to File>Options>Advanced>Send/Receive and select All Accounts then the Edit button I show the default account which appears to not really be the default with a checked box for send/receive but the Microsoft Exchange account is unchecked.
If I change the checked boxes the problem is resolved and messages go out.

I also delete the default email account since it isn't the actual account used by users. Please don't do this unless you are sure you're not actually deleting the account with all your email in it.

I'm seeing quite a lot of this happening as well and it's VERY hard to pin down.

Comment / observations:

@"xPenguinjasx"
"two seperate Email accounts pointing to my Exchange server"
> I pretty sure that scenario is already "acknowledged" by Microsoft and fixed in SP12285449 – Multiple Exchange accounts are created in Outlook 2001 when you have an existing Outlook profile after you install Office 2010.http://support.microsoft.com/default.aspx?scid=kb;en-US;2285449

IMHO this area is far too diffiuclt to troubleshoot tho.
Identifying / rule-ing add-ins in / out via a process of elimination is VERY time consuming and not always conclusive in cases where this issue only happens very "sporadically".

If an add-in is "tocuching" a mail, ideally I want to be able to try "see" this via some sort of default log / debug output / util.
It dosn't seem possible right now (if anyone knows how to get a better insight into this please advise!)

IMHO Outlook logging needs to be dramatically improved (ideally completely overhauled because it's very poor)
It's far too "difficult" to pinpoint root cause when add-ins are invovled.
(if you do ask MS one of the first things you'll get told is to eliminate 3rd party addins, but in reality most people need those so want track down an issue with this in-place)

Great - this sounds very relvent - but there is no KB article associated with this or link to additional info!
I should be able to click on a link which will tell me about the issue / explain what was fixed and make a judgement if this is relevent

Lastly - the "sledgehammer" of re-creating mail profiles.
Often this is used / resorted to, but (IMHO) people "shouldnt have to do this".
Why are mail profiles primarily binary info / black box (apart from due to "legacy" reasons)
Why isn't this info in a more accessable form allowing issues to be properly troublshooted.

I have found disabling my antivirus program temporarily allows all stuck emails to be sent. I have had to do this with both Avast anti-virus
and AVG anti-virus programs. I have had the same problem with Outlook 2007 and 2010. I don’t think it’s a Microsoft problem, just an overactive anti-virus program.

Try right button click on the message stuck in the outbox folder and select "forward". On the duplicate message that appears, press the send button. Press F9 to send/receive. Delete the stuck message from the outbox.

I have this issue (Outlook 2010) if I am disconnected from my Exchange server, send the message, then eventually connect expecting the Ooutbox to sync as other folders do. Rather, messages sent while in offline mode remain stuck in the Outbox, even
if Send/Receive is manually clicked. It ironically claims that 'This folder is up to date'. If I open up the message and click Send, still nothing happens.

To work around this, drag and drop the message(s) into another folder (i.e. Drafts) then from there open each message and click Send. This re-places it into the Outbox but in this case it now actually sends (provided you are connected to your e-mail
server). FYI this only started happening after installing Outlook 2010 SP1.

I have messages stuck in outbox (Outlook 2010) with 2 Exchange accounts. (for the second account there are "send as" persmissions).

All works, but after a few days, messages start to get stuck with error 0X8004011D when I send mails from both accounts.

The strange thing is that the status bar for one account says: "Connected to Microsoft Exchange" and when I click on the other account it just says "Connected".

When I disable cached mode for both accounts, the status bar says for one account "Online with Microsoft Exchange" and the other one "Online". But then I can send mails for the main account. The other one keeps the messages stuck in the outbox, with no error
at all.

Creating a new profile solves the issue for a few days and both accounts say "Connected to Microsoft Exchange". After a few days the same problems start over again.

I hope someone can figure this out. I already spend a lot of time on this issue. All updates are installed.

For the record, the problem as described in my post of Monday, February 21, 2011 1:04 PM still stands unsolved and unaddressed. We have tried ALL the suggested approaches here (including those posted after my original post, and that tool from
Relief that I asked about) - and none have worked.

There is clearly some bug here. I hope someone from the Office team at MS takes note.

My "ideal" from a troubleshooting perspective would be:
1) Have a way to flag / alert an item is "stuck" (e.g. noted in event log or a log file)
2) Be able to turn on some sort of debug logging showing which add-ins are "touching" the items

It's not as if this is a new issue. I remember when I had the same problem in Outlook 2003 - every once in a while mail would get stuck in the Outbox. I agree with yoshm, there is some core functionality that is broken and it has been for at least 8 years.
Work arounds are just a way of patching over something that should not happen.

It's not as if this is a new issue. I remember when I had the same problem in Outlook 2003 - every once in a while mail would get stuck in the Outbox. I agree with yoshm, there is some core functionality that is broken and it has been for at least
8 years. Work arounds are just a way of patching over something that should not happen.

In the case I am dealing with, Outlook 2003 worked OK - mail was sent when it was supposed to be. The problem of send latency (i.e., getting stuck for an indeterminate amount of time in the outbox) only started after upgrading to Office 2010.

The bug may have existed earlier, but in my case, it only showed up after the upgrade.

I'm working with Outlook 2010 32-bit and Win 7 pro 32-bit connected to an Exchange 2007 server via RPC over HTTPS. I can't even end the outlook.exe process after attempting to send an email. It works fine until I go to send/receive and click
"send all". Yes, I have the option set to send them immediately. It's a very simple message I'm sending with nothing but the word "test" in it with no signatures or attachments.

This was before and after installing Office 2010 SP1 and other Office updates. I've recreated outlook profiles. I've tested using pop instead of Exchange 2007 accounts. I've disabled all addins. I've uninstalled antivirus software
(AVG that did NOT have the email protection portion installed from the beginning). I've removed addins through the registry as suggested in a link in this thread. I've renamed the sharing.xml.obi file. I've ran repair installs on Office.
I've uninstalled and reinstalled Office and then updates before reconfiguring the outlook profile. Nothing I've done has changed the behavior... until now.

I logged on as a different user to the pc and connected to the external exchange server, sent mail, and all is working fine. To anyone else reading this threadnaught, I suggest testing it through a different windows user profile, then
renaming their windows profile, recreating, and moving data over.

But still, why does a thread have to go on for 8 months? Please fix this, Microsoft.

this problem occurs when the "sent items" file/folder is full. you can do one of the following:

delete messages from the sent items folder.

or:

you can delete the file that contains the sent items (the file with the dbx format)
if you delete it microsoft outlook will make a new blank copy. if you want to know where the file is located hold your mouse on the sent items, right click and then properties, you will see the location.

that will do it but if that don't work try archiving a good portion of mail. Last thing to check is to make sure it is using the new pst format. If you see this with a 2gb file create a new pst and export/import mail to the new pst to allow for 20gb.

This may be a resolution if you use pst files (but this is a known issue when a pst fills up, that occurs quite often where I work, for users that use psts use them only to archive old email. The psts
are not the delivery point), but we have the same issue here with messages getting stuck in the Outbox and we use Exchange accounts. All email gets delivered and stored on the servers, except personal archiving of course.

We have Outlook 2010 on XP-Pro workstations with Exchange 2010 servers.

We have users here that have well over 10,000 items in their Sent Items folder and are still able to send emails while others which have much fewer items, have the stuck email issue, so the pst issue could not be the problem.

I have done some diagnostics to try to figure it out. In one particular case, the user sent an email at 9:35 am, she noticed that the email was stuck in the Outbox, then called the help desk. By the time I got the request the email had already gone, but
I did a tracking of the message anyway to see if it showed anything. Our mailbox server never even showed the message as submitted from the client until 10:47am, more than an hour after it was sent by the user. Interestingly though, the same item in the users
sent item folder showed it being sent at 9:35am, which is when the item first arrived in the user's Outbox.

With an Exchange account, the Outbox is located on the server along with all the other folders. In another case when I used a utility this see into the users Exchange account from a different workstation, the message that was stuck in the client's Outlook
Outbox did not show up in the server outbox, so the Outlook client must be caching these messages. We do not have cached mode turned on either.

I have also noticed that when I initiate a send with the MAPI utility on the users workstation all messages on the client workstation that is affected will send.

The workaround that I have used with our clients is to have them use Outlook Web App. It does not have any issues with messages getting stuck in the Outbox. Most of our users don't like using it at the office though.

The disturbing fact here is this problem is growing, I have more and more users reporting the issue. Fortunately it is still a small percentage compared to the number of users I have. 350+

As your users have to sync so much information it is being triggered on send/receive.

There are no set limits for items, it has to do with tables in the file, I think there can be like 6090 entries per table per folder or something like that. People who send pdf attachments will be effected much more by this. I have seen users with over 13k
items do just fine, and I have seen users with 7k items who have problems.

Using a PST is far better than other options and it keeps workers productive when they are not connected to the server.

The key to your problem is in your troubleshooting; mapi send works, so explicit send works, but send/receive does not. Check your sync logs and make sure av isn't scanning mail folders on the server. The send/receive details should provide a clue as to
what is causing your sync delays.

based on your details it sounds like the offline files have been corrupted. You need to close out outlook using file>exit and make sure it isn't running in the background.

Delete your offline files and open outlook again. Exchange will download a new copy of the information to outlook.

To prevent this from happening again, you will want to set up an archive policy. I never see these problems with a company who has a working archive policy and it is enforced on all folders. NEVER EVER.

Once the files are archived and you only have current email, you can right click the folder hive and goto properties and choose to compact the file. This will remove dead space and some fragmentation from the mail files as well.

Because you said it is relieved when disconnecting the others users mail file, that isolates the problem for you. See which mail file is causing the problem and run the scanpst after making a backup if you still have the issues after archiving.

There could be an old message in one of his folders either stuck or out of sync causing the problem.

or via GPO as described in the article (assuming you actually want to enforce this)

-AL

Hello Al,

I believe the user mentioned they tried that with no success. Also their emergency requirement would be circumvented if this is used. They need to fix the problematic mailbox. That user probably has a really crappy outlook experience but doesn't complain
much about it.

Virtually all mail sent stays in the outbox for an indeterminate amount of time. We have tried all the solutions suggested in this thread prior to this date and none work. If we set "Send immediately" it still waits. We try send/receive
- completes "successfully", but the mail is still in the outbox. We go offline, online, offline, online - still stuck. We set it to send/receive every 3 minutes - 20 minutes later it'll still be in the outbox. We turned off mail scanning on the anti-virus
(AVAST!) - made no difference.

Eventually, all mail does get sent. Just not when we want it. It might be 10 minutes
later or two hours later or something in-between. This is extremely frustrating, as you can imagine.

It has nothing to do with Exchange, as there is no Exchange in the equation here - only Outlook 2010 and SMTP.

We are having a similar problem with one of our users. E-mail sits in the outbox. If you shutdown outlook ans start it up again the e-mail all gets sent. We are using pop3 and SMTP. We use Bitdefender antispam. You have to restart outlook everytime you
need to send e-mail

Thanks a million. I found an add-on that had been inserted into my Outlook 2007 when I had downloaded a free trial version of Abby Fine Reader pdf-word converter programme a few weeks ago. Removing that seems to have solved the problem. I remembered having
this same problem years ago, and again it was an 'add-on'. Hard to find add-on's in Outlook 2007, they are in something called 'Trust Center' [lol] under Tools menu. To all those frustrated senders out there: add-ons add-ons add-ons

I have been searching for days on how to delete my outbox from trying to send an email. What happened was I sent a file over to another account not realizing the file was 108M! Now I can not delete it. Using the offline method, control panel
method, I have been very unsuccessful.

Also, when I updated to MS2010, my account is showing as a file, and outlook is the primary inbox. I am not able to utilize features like " find All" or "send to junk". I have tried creating the account again under POP 3, but only able to setup
IMAP/SMTP.

After two hours of dealing with this issue and trying almost everything in this thread, I found a solution that worked instantly.

The fix is actually very simple: I decreased the MTU value in my router from 1500 to 1400 and my emails stuck in Outbox were sent immediately.

This means Outlook was trying to communicate with my SMTP server using the default packet size available in Windows (1500), but for some unexplicable reason (my DSL provider tweaking their network or what), the SMTP server was not able to accept them.

Decreasing MTU to a lower value was an instant fix in my case, give it a shot if nothing else works...

Been having the same issue with Outlook 2010 since I installed it on a new machine as part of our IT build. Happens both when I'm in the office connected directly to our LAN or external on VPN. Messages just sit there in the Outbox instead
of sending immediately like they did in OL 2007. The only workaround I found was to right click on the Outbox and select Process All Marked Headers. Everything then immediately sends. I haven't experimented much but I think the messages
eventually send if I do nothing but it's an irritating issue....

I have the same issue which started only recently, I have 3 other email addresses on the same domain which all work correctly so I am leaning towards the size of the file/folders in the problem email address. Can anyone give any advice on maximum file
sizes ?

To remove a blocked email from outbox the simplest method is to drag to 'draft' folder open and resend

I'm having the same issues as others - email getting stuck in the outbox of Outlook 2010 clients(I've seen it on 4 different machines so far), two different networks. One network uses Exchange 2010, another 2007. This happens whether they are
local, or connected using https. For the most part, I just remove Outlook 2010 and roll back to 2007(open license) and they are fine. This is specific to Outlook 2010. HELP!!!! Additionally, the Outlook clients are fully
updated(SP1 with any Office updates). Mailbox sizes vary.

Are you running an older SEP build in your environment? Make sure you are running the latest (11.0.7200.1147), some older versions did have reported issues with Outlook. You can download RU7 MP2 from Fileconnect
with a valid serial number.

If there is an attachment while using VPN and you send the e-mail and it goes into the Outbox. If you go to the outbox and hit Send/Receive it might go out if you are fast enough (I used the same message and attachments with immediate response and delayed
response -- if you delay the problem is manifest). If you open the message and hit Send there is no action, the progress of Send/Receive is shown and it shows no errors but the message is still there. Open the message and it says along the top
that the Message will not send automatically, it has acquired a delayed delivery attribute, check the options and message is set not to go till the end of the day, uncheck the delay option, save (or don't save) click the send button the message closes, Send/Receive,
message is still there. Open the message and the delay option is still on. I tried changing the time for send to some time in the past, i.e. 10:00 am and it was 11:30 am. Send/Receive. Nothing. Wait 10 min. (Set option send receive
every 2 min and saw the process go but message is stuck). Did research. Set Off-line mode, went back on-line with out effect. I repeated waiting longer -- 10 min. -- and went back on-line waited 10 min and I saw 3 of the Send/Receive processes
but still the message sat in the Outbox. Logged off the VPN, shut down the computer, brought the computer into the office and connected to the lan repeat all of the above and still no sending that message. Nothing seemed to work and connecting
to the network did not resolve it. Messages came in on the VPN and the LAN and other messages went out on the LAN -- did not try to invoke other short e-mails when I was on the VPN. I even deleted the srs file thinking something might be wrong with it.....

A poor work-around was found from others in this thread, drag the e-mail into the drafts, open the e-mail and then send. Voila. A poor voila but a voila all the same.

I've think I found a simple workaround to this problem for Outlook 2010. Go to the Options panel, then the Advanced option and check the box that says "SEND IMMEDIATELY WHEN CONNECTED" in the Send/Receive option. I tested this and it
worked GREAT. No more problem of emails getting stuck in the OUT folder with a "DATE: NONE". If you can live with your emails being sent immediately when clicking send, this is the perfect solution to this problem.
wendell simmons

For the record, the problem as I reported it here previously (originally on Feb 21, 2011 with several followups) still exists and remains unsolved and unaddressed by any of the "solutions" suggested here, all of which we have tried
:-(

I have spent a number of hours today working on a simillar issue, namely items that get stuck in the Outbox. I have pretty much established that if you open an item in the Outbox (either through the Outlook API or via the Outlook User Interface) before
it is actually sent (i.e. when in cached mode, before it gets picked up by a send/receive), it gets stuck in the Outbox folder and will never be sent until you open it and press 'Send' (again either programatically or via the Outlook user interface). I don't
know if this is the underlying issue for the symptoms documented in this thread (assuming it is not one of the other causes such as Symanetc etc) but I hope this information might help narrow your issues down.

Yeah I check with our Mail engineer techs they advised that option is enabled. This is happening to random users and at random times. The current workaround is on the desktop side Tick Schedule Send/Recieve change from 30min to 2min. Also on the Exchange
side profile the users account and set that option. The issue goes away.

Before deleting the mail profile, move the content of the Outbox into a new folder you create within the Inbox or the contents may be lost.

Close Outook

Control Panel>Mail> Delete existing profile.
Add new profile, reopen Outlook, move all of the Outbox contents back into the Oubox folder. You will then have to open each individual email within the Outbox and click "Send".

Delete the folder you created within the Inbox to temporarily store your Outbox items.

Please don't delete the pst files. It is not necessary. Go offline or use windows search to find and delete the message. you can even set a new pst as default and delete the stuck message from the old pst - but deleting the pst to get rid of a stuck message
is like throwing the baby out with the bathwater.

Hi there, look we had the same issue in our organization and we tried all the steps that appear in this site plus other ones, and the one that did work for us was much simpler than we tought, we just disabled the antivirus and disconnected the computer
from the domain, then we reconnected it to the domain, test OK, then we enabled the antivirus again, test OK, and it has worked well since then, hope this works for you, greetings from monterrey mexico.

pd: a workaround that solved our issue meanwhile was to change the pst target to our server as default instead of the pst stored in the mail folder of the user, obviously the user had to be moving the msgs from there to the other pst cuz our server has a capacity
of 200mb per user, we did this just for about 1-2 days.

Fix for this is to simply ensure you unplug network connectivity to your machine laptop or desktop no link to internet:) One step more than simply clicking working off line:)

Then simply delete the message in the outbox this worked right away after all the other solutions failed. It appears that the send feature keeps trying to send the e-mail thus blocking the delete command/move command or any other system requests.

The Message I kept receiving was the it was being transmitted.

So once I stopped the network connectivity the E-mail message was not actively trying to be sent and I was able to delete it:) Hope this helps The Ronin

I have been experiencing the "stuck in the outbox" issue for some time on a stand-alone pc with Outlook 2010. I have tried creating a new profile, repairing the .pst files, even the OLFix solution (which just corrupted my profile and forced me to create
a new one in order to get Outlook working again). None of these solutions have worked.

I have several POP3 and IMAP accounts set up in my Outlook. The default account is POP3. My outlook is set up with send/receive set to manual.

There are a few things that I have noticed, however, and was wondering if others have seen the same and if my experience will provide any further clues to this problem:

If I send an email from any account, then check the outbox, the email is there but it is not italicized as normal and is listed under "Date: None" There is no problem deleting the email; however, if I leave it in the outbox and create/send another
email, it goes into the outbox under "Date: Today", is italicized, and sends OK. If I left or right click on the good email before sending, it changes to non-italicized and moves itself into the "Date: None" category and stays there until deleted.

Yes, they actually do send if I don't look at them. That would also explain why sometimes (while looking at the outbox as I click "send" on the email compose screen) I have seen it appear italicized for a fraction of a second, then change to non-italicized
(probably the instances of this that I witnessed was for a large email which took the offender a fraction of a second to "read".

I had 7 mails stuck in the outbox after getting under my message quota. 4 sent when I clicked Send/Receive, 3 remained stuck. I Ran Unstuck Email from ReliefJet Essentials and it said it found no trouble and the mail remained.

I then tried right-clicking each email and chose Reply/All... it oppened an email that looked just like my original, addressed and dated with the current time, but they sent properly!

After searching long and hard for my answer (I never did find it) I thought I would share what fixed my problem. One user was experiencing an issue where they had messages go into their outbox, but would not send, and were not receiving any errors on send/receive,
they would just sit there. After running through all of the steps here, http://support.microsoft.com/kb/813514, and here, http://www.howto-outlook.com/howto/sendreceiveerrors.htm and quite a few others, I finally figured out that the user was
set up with her mailbox on our archive database in Exchange instead of the mailbox database. This randomly happened because the user email was working fine until a week or so ago. I compared two users in the EMC and finally picked up on it. Hope this helps
someone.

This is what I've been doing, as well. I have to remove the names of the people it's being sent to, save it in drafts, reopen it and add the names back on and send it again. It works almost without fail, but what a pain!

Thanks for the links roger, I've been struggling with this problem for months.

My emails would not send because they would immediately switch to the "Read" status (as opposed to "Unread" status) -- Outlook won't send emails in "read" status. Turns out my problem was caused by the Apple iCloud and Change Notifier add-ins.
My solution was to disable those add-ins and close and restart Outlook. After that, my emails stay in the "unread" status in the Outbox until I press "Send All" from the "Send / Receive" ribbon tab. (note: I have "Send immediately when
connected" UNchecked ... File > Options > Advanced tab > Send and receive section > "Set send and receive settings for incoming and outgoing items.")

Another work-a-round is to open Outlook in safe mode (which disables most add-ins) and send in that state. After sending emails, close out of safe mode and re-open Outlook in regular mode.

I just recently started experiencing the issue yesterday, then had the same thing happen today. Yesterday, I solved the issue when I noticed that the email in question was actually open. Once I closed the message and hit F9 (Send and Receive) the message
sent. So, this morning, when I had the same thing occur, I checked to see if the email message was open. I did not initially see it in the running task bar so I became suspicious. After about 10 minutes it mystically appeared.

Is it possible that I overlooked this, doubtful on account of recent experience. I would say the first thing you should try here is to close Outlook, then reopen it and try to manually Send/Receive.

As with any issue, always start with the simple stuff...hope this helps!

When I visited a friend for some time I found that in Outlook 2010 I could receive emails but not send. Sent items would simply sit in the Outbox not moving. It turned out that my Income Mail Server that my ISP uses could stay the same as I
was receiving mail. However I did need to change Outgoing Mail Server (SMTP) had to be changed to the SMTP setting for the ISP at my friend's house.

I'm using 2007 since my Quickbooks version 2009 send mail did not work in 2010. That said, your solution basically worked as it put the "stuck" mail from the "Sent" "NONE" status to listing it for a scheduled delivery and was sent after
the 1 minute delay I selected when setting it up. The problem thought still exists and "Send/Receive" all tab has never sent any mail even though it goes through "check off" process. It will receive but never sends any emails immediately. I'll keep looking
down the thread to see if there is a final solution. BTW I'm using pop mail, no Exchange server.

I've used Outlook 2010 for two years without ANY trouble. One morning I sent an e-mail that went out as usual, follwed immediately by another that got stuck in the outbox. It never occurred to me that my problem might be the outgoing server (SMTP)
port. I missed it in all these posts, but found a reference to it in Leo Notenboom's website. After reading about port 25 prohibitions I went to the Comcast website and did some research--they've discontinued use of port 25 for
outgoing e-mail. (Was that discontinued between my two e-mails?...) They had a fairly good "how to" that I followed and viola, I'm back in business.

I have just seen this happening for a client where we have noticed that it is only happening to the users connected over VPN and only to users connecting to the legacy Cisco VPN but not happening to the new Juniper VPN they have implemented.

I investigated a bit further and changed Outlook from using RPC connection to HTTPS by selecting the check boxes to connect using HTTP first on both slow and fast networks. This fixed the problem.

However, I only see this as a workaround and not as a solution to the underlying problem. I feel the underlying problem is related to connectivity / networking as the RPC connections works OK over the Juniper VPN and when users are on the corporate WAN.
However, I currently do not a way to prove it or to know what needs fixing. I haven't done any latency or jitter testing yet. I wonder if anyone is able to give any pointers?

In our instance, we have fixed the problem by updating the firewall configuration. SmartDefense feature of the CheckPoint firewall was blocking a connection made to port TCP/57497 on the Exchange Server.

I concur with praziquantum above. I had the same issue - Emails stuck in the outbox on Outlook 2010 - and solved it by disabling the Apple iCloud and Change Notifier add-ins. The issue certainly seems to be caused by those add-ins.

I am having an issue with this here at work. This is going to be lengthy, but maybe someone can help me out.

We have a group of users that have a department mailbox along with their personal mailbox in the Navigation Pane. Both mailboxes (on Exchange 2007) are set up as two accounts (go to File tab > Account Settings > Account Settings... and you
see them both).

Messages started getting stuck in the Outbox about 4months ago and I am not sure how to solve this. Here is what I did to troubleshoot the issue.

I removed the mailboxes and re-added them and that worked for a little bit, but the same issue came back.

I tested it out in OWA and the message is still stuck (verifying it's not the Outlook install on the PC)

Sent out multiple test messages and not a single one gets stuck in the Outbox.

Moved the mailbox to a different store, didn't fix the issue.

Verified that no one is editing the e-mails when they're in the Outbox. Users are leaving it alone as is.

The e-mails only contain text. None of the messages had attachments or any kind of images at all.

Set up separate profiles (Start > Control Panel > Mail) and tested it out that way.

Switching to Cached Mode makes the message disappear, but as soon as you revert back you still see it (I don't consider this a solution).

If anyone can assist with this or give me any kind of ideas that would be great. I'm looking to resolve this issue and get it fixed once and for all!

My problem is that the "delay send" is automatically checked on every message, and even if I remove the check mark and try to send the item it still keeps it. I delete the message and re-create it and the delay receive still checked, I even tried
changing the date on my pc to see if it would send.. did not. the only way I can get them to send is if I move the message to my inbox and then open it and hit the send button from there. then it goes. ridiculous. obviously there is a but
in my outlook 2010.

The folder needs to synchronise. This has also happened to me. In a nutshell, what happened is that I did a send/receive and logged off about 2 to 3 minutes later. The article that I'll link to says that it can take up to 30 minutes to synchronise, so when
I log off 2 or 3 minutes after sending the synchronisation has not completed. Technet is not allowing me to add the link here, but just search for kb 842284 in lieu of a link.

The KB article describes manual synchronisation. What worked for me was going back onto the computer I sent mail from, I opened a few emails and then when I saw the message at the bottom that said it was synchronising I then logged off and the messages showed
as sent.

I thought this could be the answer, because I got good results... for only a brief time. However, same problem continues. Not sure how to remove my "proposed as answer". Sorry JazzyJoe... Was this your final resolution to
this issue?

Am not on exchange server, and the problem is NOTonly for emails with attachments. Have had Outlook 2010, with my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to time
in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) transfer the
stuck emails to Drafts.

2) Reboot the computer.

3) Transfer and send each stuck email.

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

Am not on exchange server, and the problem is not only for emails with attachments. Have had Outlook 2010, with my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to time
in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) transfer the
stuck emails to Drafts.

2) Reboot the computer.

3) Transfer and send each stuck email.

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

Am not on exchange server, and the problem is not only for emails with attachments. Have had Outlook 2010, with my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to time
in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) transfer the
stuck emails to Drafts.

2) Reboot the computer.

3) Transfer and send each stuck email.

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

Am not on exchange server, and the problem is not only for emails with attachments. Have had Outlook 2010, with my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to time
in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) Transfer the
stuck emails to Drafts.

2) Reboot the computer.

3) Transfer and send each stuck email.

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

Not perfect because not everyone wants their emails sent immediately. But, then my solution is only a workaround too. This is a many years' long problem of Microsoft which THEY should address and fix, period.

Am not on exchange server, and the problem is not only for emails with attachments. Have had Outlook 2010, with my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to time
in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) transfer the
stuck emails to Drafts.

2) Reboot the computer.

3) Transfer and send each stuck email.

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

Am not on exchange server, and the problem is not only for emails with attachments. Have had Outlook 2010, with my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to time
in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) transfer the
stuck emails to Drafts.

2) Reboot the computer.

3) Transfer and send each stuck email. (You can resend them all at once, but I've done one at a time until I know it's working.)

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

Am not on exchange server, and the problem is not only for emails with attachments. Nor is it only for reply emails, but for
originated new emails as well. Have had Outlook 2010, with my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to
time in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) Transfer the
stuck emails to Drafts.

2) Reboot the computer.

3) Transfer and send each stuck email. (You can resend them all at once, but I've done one at a time until I know it's working.)

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

Am not on exchange server, and the problem is not only for emails with attachments. Nor is it only for reply emails, but for originated new emails as well. Have had Outlook 2010, with
my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to time in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) Transfer the
stuck emails to Drafts. (Just as a safeguard so as not to lose them.)

2) Reboot the computer.

3) Transfer and send each stuck email. (You can resend them all at once, but I've done one at a time until I know it's working.)

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

Am not on exchange server, and the problem is not only for emails with attachments. Nor is it only for reply emails, but for originated new emails as well. Have had Outlook 2010, with
my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to time in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) Transfer the
stuck emails to Drafts. (Just as a safeguard so as not to lose them.)

2) Reboot the computer.

3) Transfer and send each stuck email. (You can resend them all at once, but I've done one at a time until I know it's working.)

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

I have office pro plus 2010 and I have been using it since mid 2011 without any problems at all, in particular as the one described above.

About a week or so ago I noticed my emails were getting moved to the outbox instead of being sent directly as was the case in the past. I know that I have made NO changes whats so ever to my outlook configuration.

EXCEPT FOR ONE THING !! I recently downloaded and installed Norton 360 30 day trial..

I have just removed the 360 trial and cleaned out the directories of all references and restarted my computer, opened outlook and tested a number of emails i had trouble with and they all worked as before...

No Norton 360 and outlook works fine.. All messages are sent immediately, as before.

I am going to re install my previous internet security suite and test it for a week and post the results for you.

This may or may not be of any help you you but thus far my outlook is functioning as per normal.

OK, I've JUST FIXED THIS ISSUE on my PC - this may or may not work for you.

I am running Win7 - Outlook 2010 - Norton 360

Solution:
Open Norton 360
Settings > AntiSpam > Turn it OFF!

I restarted outlook, unfortunately the mails that were stuck with "Date:None" remained, so I deleted these and tried re-sending my emails again as new mails and they sent straight away (momentarily passing through outbox).

I now have instant Sending happening when I compose a mail message

My thoughts on this are; Norton uses 'Protected ports' 25 and 110 - however, my mail server uses different incoming and outgoing ports and I was unable to add these as protected ports in Norton getting a message similar to "These ports are in use by another
program and cannot be protected". I believe that Norton AntiSpam is blocking mail on any port it isn't capable of protecting. I assume if I was using ports 25 and 110 that it would work (though I haven't tried this).

Choose Send/Receive tab and in the download section, click cancel all. Or open the Outbox folder and at the outer edge near the bottom of outlook you will see the sending message. Click and than cancel, now you can delete the email.

I understand this is a very dated post but I wanted to offer my two bits. Most recently I had a situation where my Outlook 2010 would have messages stuck in the outbox. All the advice given is solid but I would add one more thing. After performing
all the recommended procedures (including deleting and recreating the outlook profile) I finally deleted the old Outlook profile folder. Actually, I renamed it. So, perform the following:

In my case the problem was caused by the automapping function in outlook/exchange.
When you give someone full access permissions on another mailbox, that mailbox automaticly gets listed to outlook.
If you also manually add this mailbox to outlook those two conflict.

It can work for a couple of hours, days weeks but eventually mails get stuck in outbox.

you need to edit the user accounts in the Active Directory and remove your name from the MsExchDelegateListLink attribute from the mailbox you want to add to your outlook.

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